Keepers of Tradition & Culture in Travel

Tuscany & Umbria

Etruscan Wine Trails: Viticultural Journey Through Tuscany & Umbria

8 Days

Join us for an exclusive Small Group Tour Tuscany and Umbria during the Annual Harvest, where vineyards, wine cellars, and breathtaking landscapes come together for an unforgettable experience. This 8-day journey is crafted for wine enthusiasts of all levels and guided by two expert sommeliers who will enrich your appreciation of wine through tastings and an in-depth look at the winemaking process.

In Tuscany’s picturesque Val d’Orcia, you’ll explore historic hilltop towns such as Orvieto, Todi, and Montefalco, each steeped in Etruscan heritage. Alongside wine, indulge in the region’s famed truffles and savor delectable local cuisine that reflects the essence of the “slow food” movement. This Small Group Tour Tuscany is designed to showcase the best of the region’s culinary and cultural treasures.

Accommodations include stays in historic properties, such as a Renaissance castello once owned by Catherine de Medici and a charming palazzo surrounded by vineyards. The itinerary aligns with the Montefalco Wine Festival, offering the unique opportunity to meet local producers and immerse yourself in their passion for winemaking.

Highlights of the tour include sommelier-led workshops, winery visits with tastings, guided tours of Civita di Bagnoregio and Assisi, an exciting truffle-hunting experience, and a hands-on cooking class to master traditional Tuscan and Umbrian dishes. With private transfers and a dedicated sommelier guide and translator, every detail is thoughtfully arranged to ensure your enjoyment and comfort.

Our team, experts on Italy and deeply familiar with Tuscany and Umbria, is eager to share our insider knowledge with you. This Small Group Tour Tuscany offers an intimate and immersive way to experience the very best of this world-renowned region, leaving you with lasting memories of its beauty, flavors, and traditions.

Want to Learn More About This Trip?

What’s Included?
  • 3 nights at I Borghi dell’Eremo in Umbria
  • 4 nights at Villa Le Prata Wine Resort in Tuscany
  • Sommelier workshops
  • Winery Visits & Tastings
  • Montefalco Wine Festival
  • Guided visit to Civita di Bagnoregio and Assisi
  • Guided visit of Orvieto
  • Cooking Class
  • Guided hike
  • 7 breakfasts, 3 lunches, 7 dinners
  • Private transfers for all activities
  • Private airport transfers from/to FCO
  • Sommelier guide & translator
  • Airfare – should be arranged to Rome (FCO)
  • Gratuities – we kindly ask you to acknowledge the service for your guides and driver
  • Alcoholic beverages – all alcoholic beverages except for wine included during wine tastings and meals need to be paid separate
  • Additional meals
  • Additional spa services
  • Additional excursions – if time allows, there are many more amazing sights and experiences for you to explore

Meet Your Guide(s)

Dana Beninati

Dana, host of Dine with Dana and Food Network’s Resident Sommelier, blends her expertise as a chef and sommelier to make food and wine approachable. With an MBA from Cornell and Michelin-star training, Dana shares her passion for Italian cuisine and wine across Food Network, NBC, and in publications like Bon Appetit. Based in Manhattan, she’s happiest exploring Italy’s flavors with a wine opener and camera in hand.

,
Samuele Calistri

Samuele, sommelier and founder of CalistriWines, blends his deep expertise in oenology with hands-on experience across vineyards in Italy, France, and Germany. Returning to his roots in Caprarola, Samuele now leads the historic Trattoria del Cimino da Colombo, where he shares his passion for both local and international wines, earning the Wine Spectator Restaurant Award for his curated selection. As a judge for esteemed competitions like La Guide Hachette des Vins and the International Wine Challenge, Samuele brings a piece of his global journey back to his homeland, sharing his knowledge and love for wine.

,
Karen Costa Hattaway

Karen, native to Rome, is the founder of LBR. Her mission of preserving culture and tradition has allowed her to meet extraordinary small wine makers all over Italy who share in her values. She’s excited to share these beautiful regions, along with their wine and culinary delights, with her travelers!

Departures Available
September 14-21, 2025
Starting at
€ 6.500
Single Occupancy Adjustment
€1.500
Maximum Group Size
10 Travelers

Meet Your Guide(s)

Dana Beninati

Dana, host of Dine with Dana and Food Network’s Resident Sommelier, blends her expertise as a chef and sommelier to make food and wine approachable. With an MBA from Cornell and Michelin-star training, Dana shares her passion for Italian cuisine and wine across Food Network, NBC, and in publications like Bon Appetit. Based in Manhattan, she’s happiest exploring Italy’s flavors with a wine opener and camera in hand.

,
Samuele Calistri

Samuele, sommelier and founder of CalistriWines, blends his deep expertise in oenology with hands-on experience across vineyards in Italy, France, and Germany. Returning to his roots in Caprarola, Samuele now leads the historic Trattoria del Cimino da Colombo, where he shares his passion for both local and international wines, earning the Wine Spectator Restaurant Award for his curated selection. As a judge for esteemed competitions like La Guide Hachette des Vins and the International Wine Challenge, Samuele brings a piece of his global journey back to his homeland, sharing his knowledge and love for wine.

,
Karen Costa Hattaway

Karen, native to Rome, is the founder of LBR. Her mission of preserving culture and tradition has allowed her to meet extraordinary small wine makers all over Italy who share in her values. She’s excited to share these beautiful regions, along with their wine and culinary delights, with her travelers!

Explore Medieval Hilltop Towns

Tuscany and Umbria are filled with charming medieval hilltop towns that feel like stepping into a storybook. Stroll along cobblestone streets, enjoy the views over rolling vineyards, and soak up the history in these atmospheric villages.

Wine Tasting in Chianti

Chianti’s vineyards are a must for wine lovers. Here, you’ll get a taste of the region’s famous reds, grown right in the heart of Tuscany. Each glass offers a bit of local flavor and tradition, perfect for those looking to enjoy the best of Italian wine.

Savor Farm-to-Table Cuisine

Tuscany’s farm-to-table cuisine highlights the region’s fresh, local ingredients. From artisan cheeses to seasonal vegetables and handmade pastas, every meal is an opportunity to experience authentic Tuscan flavors in a relaxed, welcoming setting.

Visit Iconic Renaissance Sites

Italy’s Renaissance sites, from the art-filled streets of Florence to the historic beauty of Assisi, offer a look into a world of masterpieces and historic architecture. These landmarks are ideal for those curious about Italy’s rich artistic past and cultural legacy.

Rich, Meaningful, Memorable Travel Awaits

Life Beyond the Room (LBR) is a sensorial™ travel concierge dedicated
to creating custom, unique itineraries for travelers seeking authentic experiences
immersed in the lifestyle, flavors, and culture of each region. Our local managers live in the destination countries and speak the local languages, allowing us to create incredible partnerships so our travelers can step off the beaten path, beyond the hotel room, and discover places unknown to most tourists.

Our commitment to sustainability ensures that your impact is positive. You will have the trip of a lifetime while making a long-lasting positive impact on the places you visit and the people you encounter. You will meet as a guest and leave as a friend! If you have questions about this group trip or are interested in custom travel design, don’t hesitate to contact us!

Group photo of Life Beyond the Room's Preferred Travellers

Preferred Traveler Program

The Life Beyond the Room preferred traveler program allows our frequent travelers to pay for their trips over time via a monthly subscription. Perks include discounts, access to exclusive destinations, and more!

Credits never expire and can be redeemed at any time towards a small group trip of your choice or any custom trip!

Group photo of Life Beyond the Room's Preferred Travellers